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Check prices for these dates

Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan
In one month
6 Feb - 8 Feb
In two months
6 Mar - 8 Mar

Our top choices for Westchester bed & breakfast

Private kitchen
The Sono Chicago

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (487)
"The Sono was welcoming, clean and very comfortable. It was easy to find and provided parking! We would absolutely stay here again and would recommend it to friends. "
United States
Ellen
The price is AED 489
AED 574 total
includes taxes & fees
12 Jan - 13 Jan
The Sono Chicago
Staircase
The Publishing House B&B

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (191)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is AED 657
AED 742 total
includes taxes & fees
29 Jan - 30 Jan
The Publishing House B&B
Living area
Dorothy's

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.4 out of 10, Very Good, (99)
"Can’t beat the price or location. Everything seemed clean and I loved the waffles. "
United States
Ashley
The price is AED 166
AED 323 total
includes taxes & fees
20 Jan - 21 Jan
Dorothy's
Double Room, Private Bathroom (Venetian) | Terrace/patio
The Villa Toscana

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (628)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
The price is AED 131
AED 300 total
includes taxes & fees
12 Jan - 13 Jan
The Villa Toscana
Courtyard
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (497)
"Nice shared spaces"
United States
Erica
The price is AED 363
AED 645 total
includes taxes & fees
13 Jan - 14 Jan
House 5863 - Chicago Bed and Breakfast
Property entrance
Wicker Park Inn

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (257)
"Fantastic location, spotlessly clean room, and a very comfortable bed. I have stayed here several times and will continue to do so."
United States
Jeffrey
Wicker Park Inn
Spa
Ray's Bucktown B&B

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (385)
"We had the best stay at Rays and will definitely be back! Everything about this place is fantastic, its hard to know where to begin, but the care and love put into their B&B can be felt for real. And had an unbelievably comfy and restful sleep. Woke up feeling refreshed, and had the best made to order breakfast!"
United States
Kristin
Ray's Bucktown B&B
Lobby sitting area
Villa D' Citta

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (113)
"Great place"
United States
Jeffrey
The price is AED 756
AED 888 total
includes taxes & fees
19 Jan - 20 Jan
Villa D' Citta
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (122)
"The room was gorgeous and well-kept, the kitchen with shared amenities (Microwave, etc) was open and accessible in a beautifully decorated and maintained common area, and our host was delightful and warm. Highly pleasant and recommended experience!"
United States
Peter
The price is AED 848
AED 942 total
includes taxes & fees
13 Jan - 14 Jan
Harvey House Bed & Breakfast
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Westchester Hotel Reviews

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"Had great rooms was very happy with Alfie and how he answered all my questions and made sure I was happy and comfortable. Thank you Alfie for making my stay amazing. "
Nancy 8-night trip
Posted 6 hours ago
LondonHouse Chicago, Curio Collection by Hilton

Frequently asked questions

Searching for B&Bs in Westchester?
Whether you're on a family vacation and want a small, cozy place to stay, or you're traveling solo and hoping to meet fellow tourists, B&Bs can be a great choice for many travelers. If you're interested in discovering some top attractions, Wrigley Field and Michigan Avenue are worth a stop.
Why consider B&Bs instead of traditional hotels?
With attentive service, opportunities to mingle with other guests, and of course a full breakfast to start the day, B&Bs offer a truly one-of-a-kind environment.
What are the best B&Bs in Westchester?
Here are some well-liked B&Bs in the area: Dorothy's: 7 rooms. 13.6 mi (21.9 km) from the heart of Westchester.The Villa Toscana: 9 rooms. 13.6 mi (21.9 km) from the downtown core. House 5863 - Chicago Bed and Breakfast: 7 rooms. Situated 14.7 mi (23.6 km) from the heart of Westchester. Enjoy the designer toiletries and private yard. Ray's Bucktown B&B: 11 rooms. 11.3 mi (18.2 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. The Sono Chicago: 7 rooms. Located 13 mi (20.9 km) from the core of Westchester. Enjoy the rooftop terrace and fireplace in the lobby.
What's the best time of year to book my B&B in Westchester?
When you're planning your getaway to Westchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What is there to do in Westchester?
Travelers enjoy Westchester for its restaurants and shopping. You might also consider a trip to sites like Wrigley Field or Michigan Avenue if you have time to see more of the area.
How can I get to and around Westchester?
You can map out your trip in and around Westchester ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 8.4 mi (13.4 km) away from the heart of the city. Otherwise, you can search for flights to Chicago O'Hare Intl. Airport (ORD), which is 8.9 mi (14.3 km) away. If you'd like to explore around the area, you may want a rental car for your journey.